Would anyone be willing to tell me which specific debts George Boleyn was preoccupied with during his time in prison?
Sir William Kingston wrote to Cromwell regarding George Boleyn's troubled conscience on the 16th May (LP x. 890) and again (LP x. 902), probably also the 16th, and this was to do with George's worry concerning his debts and his support of the promotion of a monk to be Abbot of Valle Crucis Abbey. He wanted to ensure that if the abbey was dissolved that the Abbot would be given financial help so he asked Kingston to ask Cromwell to intercede with the King. George also mentioned the Bishop of "Develyn". Kingston does not mention who George owed money to and Chapuys, in his account of George's trial says:-
"Her brother, after his condemnation, said that since he must die, he would no longer maintain his innocence, but confessed that he had deserved death. He only begged the King that his debts, which he recounted, might be paid out of his goods." LP x.908
Again not mentioning who George owed money to. I'm sure that they would have been gambling debts so would have been friends and courtiers.
He would obviously have also been worried about his wife, Jane, and after his execution Jane wrote to Cromwell "Beseeching him to obtain from the King for her the stuff and plate of her husband. The King and her father paid 2,000 marks for her jointure to the earl of Wyltchere, and she is only assured of 100 marks during the Earl's life, "which is very hard for me to shift the world withal." Prays him to inform the King of this." LP x. 1010